Kiely and coworkers in U.S. Pat. No. 4,833,230 and copending application "An Improved Process for Making Activated Aldarate Esters, Ester/Lactones" of even date herewith describe general methods for preparing polyhydroxypolyamides from aldaric acids, including poly(glucaramides) from D-glucaric acid. In that process, activated glucaric acid molecules are reacted with diamines via condensation polymerization to produce poly(glucaramides).
The D-glucaric acid monomer units (I) in a poly(glucaramide) ##STR1## are not symmetrical. The C-2 to C-5 carbon atoms in the D-glucaric acid are chiral carbons and employing the Cahn-Prelog-Ingold Sequence Rules are configurationally designated as R,C-2-S,C-3-S,C-4-S,C-5. C-1 is labelled as the "head" in the D-glucaric acid and C-6 is labelled as the "tail" carbon in the D-glucaric acid monomer unit. The process of Kiely et al. does not indicate nor ensure the order in which the glucaric acid units are placed in the poly(glucaramide); i.e. the method of synthesis does not control that stereoregularity of the condensation process. Consequently, the resulting polymers would be expected to have a random or somewhat random head-tail order of a D-glucaric acid unit with respect to other D-glucaric acid units within the polymer. Stereoregular head to tail poly(glucaramides) containing D-glucaric acid units aligned-[tail-glucaroyl-head----amine]-.sub.n, where "glucaroyl" is (I) above, have not been described in the art.